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Carubicin

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Synopsis

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Chemistry

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Also known as: Carubicin, 39472-31-6, Carminomycin i, Karminomycin, 50935-04-1, Carubicin [inn]

Molecular Formula

C₂₆H₂₇NO₁₀

Molecular Weight

513.5 g/mol

InChI Key

XREUEWVEMYWFFA-CSKJXFQVSA-N

FDA UNII

E7437K3983

A very toxic anthracycline-type antineoplastic related to DAUNORUBICIN, obtained from Actinomadura carminata.

1 2D Structure

Carubicin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-4,6,9,11-tetrahydroxy-8,10-dihydro-7H-tetracene-5,12-dione

2.1.2 InChI

InChI=1S/C26H27NO10/c1-9-21(30)13(27)6-16(36-9)37-15-8-26(35,10(2)28)7-12-18(15)25(34)20-19(23(12)32)22(31)11-4-3-5-14(29)17(11)24(20)33/h3-5,9,13,15-16,21,29-30,32,34-35H,6-8,27H2,1-2H3/t9-,13-,15-,16-,21+,26-/m0/s1

2.1.3 InChI Key

XREUEWVEMYWFFA-CSKJXFQVSA-N

2.1.4 Canonical SMILES

CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)O)O)(C(=O)C)O)N)O

2.1.5 Isomeric SMILES

C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)O)O)(C(=O)C)O)N)O

2.2 Other Identifiers

2.2.1 UNII

E7437K3983

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Carminomicin

2. Carminomycin I

3. Carminomycin Ii

4. Carminomycin Iii

5. Carubicin

6. Carubicin Hydrochloride

7. Demethyldaunomycin

8. Demethyldaunorubicin

9. Hydrochloride, Carubicin

10. Karminomicin

11. Karminomycin

12. Nsc 180,024

13. Nsc 180024

14. Nsc-180,024

15. Nsc-180024

16. Nsc180,024

17. Nsc180024

18. Rubeomycin A

19. Rubeomycin A1

2.3.2 Depositor-Supplied Synonyms

1. Carubicin

2. 39472-31-6

3. Carminomycin I

4. Karminomycin

5. 50935-04-1

6. Carubicin [inn]

7. O-demethyldaunomycin

8. Carminomicin I

9. Nsc-180024

10. Ccris 961

11. Chebi:31359

12. Dsstox_cid_2742

13. Dsstox_rid_76711

14. Dsstox_gsid_22742

15. Karminomitsin

16. Ncgc00159344-02

17. 50935-04-1 (free Base)

18. (7s,9s)-9-acetyl-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-4,6,9,11-tetrahydroxy-8,10-dihydro-7h-tetracene-5,12-dione

19. E7437k3983

20. (8s,10s)-8-acetyl-10-(((2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-1,6,8,11-tetrahydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione

21. Carubicina

22. Carubicine

23. Carubicinum

24. (1s,3s)-3-acetyl-3,5,10,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranoside

25. (7s,9s)-9-acetyl-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4,6,9,11-tetrahydroxy-8,10-dihydro-7h-tetracene-5,12-dione

26. 5,12-naphthacenedione,8-acetyl-10-[(3-amino-2,3,6-trideoxy-a-l-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-, (8s,10s)-

27. Cas-50935-04-1

28. Carubicine [inn-french]

29. Carubicinum [inn-latin]

30. Carubicina [inn-spanish]

31. Ccris 6185

32. Unii-e7437k3983

33. Ncgc00160675-01

34. Carminomycin; Carubicin

35. Carubicin [mi]

36. Schembl9552

37. Chembl474260

38. Dtxsid3022742

39. Ex-a2244

40. Hy-b2171

41. Zinc4654755

42. Tox21_111589

43. Tox21_111978

44. Bdbm50103635

45. (1s,3s)-3-acetyl-1,2,3,4,6,11-hexahydro-3,5,10,12-tetrahydroxy-6,11-dioxo-1-naphthacenyl-3-amino-2,3,6-tridesoxy-alpha-l-lyxo-hexopyranosid

46. Cs-0021097

47. Carminomycin, O-demethyldaunomycin, Ccris 961

48. 935c041

49. A857268

50. Q5047474

51. (1s,3s)-3-acetyl-1,2,3,4,6,11-hexahydro-3,5,10,12-tetrahydroxy-6,11-dioxo-1-naphthacenyl 3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranoside

52. 5,12-naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-, (8s-cis)-

53. 5,12-naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-, (8s-cis)-

54. 5,12-naphthacenedione, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-, (8s,10s)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₇NO₁₀
Molecular Weight	513.5 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	3
Exact Mass	513.16349606 g/mol
Monoisotopic Mass	513.16349606 g/mol
Topological Polar Surface Area	197 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	944
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Topoisomerase II Inhibitors

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

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